239094-36-1

Basic information

• Product Name: ethyl-3-hydroxy-2-diazo-3-(4-bromophenyl)-propanoate
• Synonyms: ethyl-3-hydroxy-2-diazo-3-(4-bromophenyl)-propanoate
• CAS NO: 239094-36-1
• Molecular Weight: 299.124
• Mol File: 239094-36-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: ethyl-3-hydroxy-2-diazo-3-(4-bromophenyl)-propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl-3-hydroxy-2-diazo-3-(4-bromophenyl)-propanoate(239094-36-1)
• EPA Substance Registry System: ethyl-3-hydroxy-2-diazo-3-(4-bromophenyl)-propanoate(239094-36-1)

Safety Data

• Hazardous Substances Data: 239094-36-1(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 17145-48-1 ethyl 2-diazo-2-(trimethylsilyl)acetate 

Downstream Products

• 1591911-92-0 C₂₂H₁₉BrFeN₂O₄ 
• 26510-95-2 ethyl 4-Bromobenzoylacetate 

Relevant articles and documents

Highly efficient and chemoselective direct aldol reaction of acyldiazomethane with aldehydes promoted by MgI2 etherate

Direct aldol condensation of various aromatic, heteroaromatic, α,β-unsaturated aldehydes and aliphatic aldehydes with acyldiazomethane was realized using MgI2 etherate (MgI2·(Et2O)n) as a promoter in the presence of diisopropyl amine (DIPEA) in excellent yields in a short time under mild conditions with high chemoselectivity. Iodide counterion, and a non-coordinating less ploar reaction media (i.e., CH2Cl2) are among the critical factors for this unique reactivity.

Safe generation and direct use of diazoesters in flow chemistry

A safe and fast method for the production of β-hydroxy-α- diazoesters in continuous flow technology is described. The synthesis involves the formation of ethyl diazoacetate in situ and the addition to several aldehydes in a two-step continuous flow microreactor setup. Rhodium acetate catalyzes a subsequent 1,2-hydride shift to give access to β-keto esters in a three-step sequence. Georg Thieme Verlag Stuttgart · New York.

Tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions

A mild and convenient method for the condensation of ethyl diazoacetate (EDA) with aldehydes catalyzed by tert-BuOK under solvent-free conditions was developed. The corresponding α-diazo-β-hydroxy esters were further converted into β-ketoesters through palladium-catalyzed 1,2-hydrogen migration under neat conditions. The two-step transformation exemplifies a simple method for the efficient and green synthesis of β-ketoesters. The Royal Society of Chemistry 2013.